A Night At the Asbury/Halloween 2017

Halloween, trick or treating, and carved out blumpkins are on the agenda:   Now, parallel to my efforts to pull a piece for Friday night, I also schemed up a way to find a cushy landing for this Halloween Eve’s eve: A hostess from a bar I went to last year in Asbury Park on… Read more

A Race to Friday Night

Big night coming up on Saturday (10/28/2017): Halloween in Asbury Park, NJ.  Now, how to best fill my Friday night before the show: So, I oiled up my Tinder and Bumble profiles until they were ready to go: So, I started my swiping on Monday.  After each match rolled in I’d start a conversation.  And… Read more

Philly for a Philly

I mentioned in last time’s disaster that I was taking a trip to Philly for business.  They say it’s unwise to shit where you eat, but the jury’s still out on eating where I shit.  And I’m ready for that business dinner. In Fall 2017 I’m making some last-minute preparations for Philly, flab-free, with my… Read more

Bartenders, Top of the Pounding Food Chain

I’ve been after this bartender for some time now.  After my initial move did not pan out, I asked the Grand Daddy Dating Poobah, who I wrote about in my Bartender and Catfish blog, how he would attempt this feat.  I will go to this man for advice on this topic at any time since… Read more

Wedding Ring Night

I love social experiments, and not too hard to find a little inspiration. The goal of this mission is simple: To test out the theory that being a married man is no obstacle to getting play. I prefer not to call myself a blogger but, rather, a playwright, since I aim to spin works of… Read more

The Bartender and The Catfish

The memory of the bartender who I met in Operation ONS stuck out in my mind like a girl using proper grammar on her Tinder bio.  I signaled to my favorite town bouncer that the lothario stampede will be coming through in just a few short days: Of course, I was being tongue in cheek,… Read more


I had recently reconnected with an old friend on Facebook in September 2017.  Shortly after that, I received a friend request from a person in common to both of us: His wife’s sister.  Meet Indiana: Indiana, from Indiana, has a stereotypical midwestern look.  Not what I’m going for, but with blue eyes, piercings, and tatts… Read more

Operation ONS

Operation One Night Stand (Operation ONS; 8/19/2017) My dating life agenda for the 973 operates in the following manner: Sunday is swipe day, where I load up a new deck of Bumble and/or Tinder girls Reserve one weekend night for a date (or two) Reserve the other weekend night for trying to pick chicks up… Read more

Blog Zero

My name is David Shepard.  I’m a 40-year-old divorcee from New Jersey.  It took a lot of work to get here.  Here is a blog about my awesome dating life.  Enjoy. Context The thing about context is, where do you begin?  I could start with marriage, divorce, any point in my two years after my… Read more